DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 05/16/2025 has been entered.
Response to Amendment
Applicant’s amendments filed on 05/16/2025 has been considered and are accepted. Claim 1 has been amended to remove “a phenyl group” from the Markush group comprising R1. Claims 1, 3-6, 8-11, 13-16, and 18-20 are now pending in the application.
Response to Arguments
Applicant’s arguments, pages 8 and 9 of the remarks filed 05/16/2025, regarding the 35 USC 103 rejection of presently amended Claims 1 and 11 over Nihashi (US Patent No 10,788,754) in view of Hatakeyama (US 2021/0048746) have been considered but are not persuasive and therefore the rejections of the prior office action are maintained. Applicant argues that Nihashi neither discloses nor suggests a quencher being a sulfonium salt of a fluoroalcohol having the structure general formula (1) of the amended Claim 1. However, the Examiner disagrees as the primary reference Nihashi may be used for all that it discloses not just disclosed embodiments therein. In part, Examiner points to the general disclosure of the compound (B) is preferably a compound represented by the General Formula (B1): (Rx)n2–X+ Ry–A- (Col 42, Ln 22-30). Examiner notes that Applicant is arguing that the Ry group of general formula B1 would not satisfy the claimed formula (1). The disclosed compound (B) comprises A- represents an organic acid anion, X+ represents a nitrogen cation, a sulfur cation, or an iodine cation, Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group, and Rx represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group (Col 42, Ln 30-43). Furthermore, Nihashi discloses that in the description of the present invention, in the case where a group is denoted without specifying whether substituted or unsubstituted, the group includes a both a group having no substituent and a group having a substituent (Col 4, Ln 35-44). The compound B-6 of Nihashi satisfies the General Formula (B1) wherein Ry is an aralkyl group substituted with fluorine atoms (forming the two CF3 groups of the claimed formula (1)), and since Ry of Nihashi may also be an alkyl, one of ordinary skill would envision simple fluorinated alkyl groups (1 to 6 carbons or so) to have similar properties. See the detailed action below.
An additional grounds of rejection is made over Hatakeyama-2 (US 2018/0004087) to teach additional limitations of the repeating units in Claims 1, 3-5.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1, 3-6, 8-11, 13-16 and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Nihashi (US Patent No. 10788754) in view of Hatakeyama (US 2021/0048746).
Regarding Claim 1, Nihashi teaches a radiation-sensitive resin compositions (abstract) comprising an acid generator being a sulfonium salt of a sulfonate ion bonded to a polymer main chain (Polymer A-17 on Col 17, Ln 50 as shown below). The actinic ray-sensitive or radiation-sensitive composition comprises a compound (B) which is capable of forming a polar interaction with the polar group of the resin (A’) (Col 42, Ln 6-10). The compound (B) is not particularly limited as long as it is capable of forming a polar interaction with the resin (A’) (Col 42, Ln 15-16). The compound (B) is preferably a compound represented by the General Formula (B1): (Rx)n2–X+ Ry–A- (Col 42, Ln 22-30). A- represents an organic acid anion, X+ represents a nitrogen cation, a sulfur cation, or an iodine cation, Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group, and Rx represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group (Col 42, Ln 30-43). Furthermore, Nihashi discloses that in the description of the present invention, in the case where a group is denoted without specifying whether substituted or unsubstituted, the group includes a both a group having no substituent and a group having a substituent (Col 4, Ln 35-44). Some disclosed examples of the compound (B) are described in the working examples through the compounds B-5 to B-8, shown below, which comprise organic anions of hydroxide anion, carboxylate anion, and fluorinated alkoxide anion and organic cations of ammonium cation, sulfonium cation, and iodonium cation (Col 112, Ln 1-35). The compound B capable of forming a polar interaction with the resin A enables a neutralization interaction that improves resolution and LWR, which is similar to the function of a quencher (Col 6, Ln 12-22). The compounds B-6 and B-8 are both used in exemplified formulations as shown in Table 3 (Col 117-118) that showed excellent sensitivity, resolution, LWR performance, and local pattern dimension uniformity (Col 121, Ln 35-40). Compound B-6 satisfies where R1 represents a phenyl group and compound B-8 satisfies where R2-R4 are hydrocarbyl groups having 4 carbons; this structure satisfies the general formula B1 where Ry is an aralkyl group substituted with fluorine atoms. Compound B-8 satisfies the sulfonium cation where R2 to R4 are hydrocarbyl group having 4 carbons. Nihashi further discloses the Rx groups may comprise alkyl groups of 1 to 20 carbons (Col 43, Ln 10-15), cycloalkyl groups (Col 43 Ln 19-30), aryl groups (Col 43, Ln 31-34), aralkyl groups (Col 43, Ln 35-39), and heterocyclic groups (Col 43, Ln 40-47), all of which may further have a substituent (Col 43, Ln 49-51) (pertaining to the R2 to R4 groups).
Regarding the acid generator, Nihashi further discloses the compound (C) capable of generating acid by actinic rays or radiation is a photoacid generator (Col 47, Ln 45-53), and compound (C) may be a low molecular weight compound or may be incorporated into part of a polymer and further a form of low molecular weight compound and a form incorporated into a part of a polymer may be used in combination (Col 47, Ln 54-58). Nihashi exemplifies one example of a polymer comprising a photoacid generator in Polymer A-17, which is a sulfonium salt of a sulfonate ion bonded to a polymer main chain (Col 107-108).
Nihashi does not teach a quencher of the general formula (1) comprising a fluorinated alcohol anion with a sulfonium cation. However, Nihashi is good for all that it discloses pertaining to the compound B capable of forming a polar interaction with the polymer resin.
Nihashi discloses all of the elements of the quencher separately but not disclosed in a single embodiment. The general formula B1 discusses the counteraction of the compound (B) may be a nitrogen cation, a sulfur cation, or an iodine cation. Furthermore, the group Ry may represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group which may have a substituent. Rx groups may comprise alkyl groups of 1 to 20 carbons, cycloalkyl, aryl, aralkyl, and heterocyclic groups. Thus, it would have been obvious for one of ordinary skill in the art to have substituted the ammonium cation of B-6 with the sulfonium cation of B-8 and to have substituted the fluorinated aralkyl group of the anion in B-6 with a fluorinated alkyl group based on the disclosure of the general formula B1 of Nihashi. While Nihashi is silent to the particular number of carbons present in the alkyl group, one of ordinary skill would look towards the simplest alkyl groups, such as alkyl groups with 1 to 6 carbons in lieu of evidence demonstrating otherwise. One of ordinary skill would envision such a modification of B-6 to produce a fluorine-substituted alkyl group such that R1 could be fluorine or an unsubstituted or fluorine substituted alkyl group having about 1-3 carbons.
It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose…[T]he idea of combining them flows logically from their having been individually taught in the prior art. In re Kerkhoven, 205 USPQ 1069 1072. In the instant case, it would have been obvious to one of ordinary skill in the art to obtain a quencher salt comprising the claimed limitation of general formula (1) and arrive at the instant claims through routine experimentation.
Nihashi does not teach the acid generator being a sulfonium salt of a sulfonate ion bonded to a polymer main chain having formula (a1) or (a2).
Furthermore, Hatakeyama discloses polymer 3 on page 90 having a sulfonate bonded to the main chain with a sulfonium cation (structure shown below). The monomer satisfies the general formula (a1) where RA is methyl, Z1 is an ester bond, Z2 represents -Z21-C(=O)-O- where Z21 is a 8 carbon hydrocarbylene group containing an ester bond, and Z3 is 2,2,2,-trifluoro-1,1-ethanediyl group. The bound photoacid generator is capable of generating sulfonic acid (paragraph [0046]).
Nihashi discloses the photoacid generator may be bound to a polymer chain and Hatakeyama discloses other polymer-bound sulfonate ion sulfonium salt photoacid generator resins. It would have been obvious for one of ordinary skill in the art to have substituted the onium salt polymer of Nihashi with the onium salt polymer of Hatakeyama through routine experimentation. The onium salt-containing polymers perform the same function as a photoacid generator bound to a polymer chain and their substitution would result in the predictable result of a base resin capable of generating acid upon irradiation to light.
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Regarding Claim 3, the discussion of Claim 1 is relied upon as above. Hatakeyama further discloses in the Polymer 3 used above repeating units comprising the general formulas (b1) and (b2) (page 90). A methacrylate monomer disclosed below in Polymer 3 satisfies where RA is methyl, Y1 is a single bond, and R11 is an acid labile group. A second methacrylate monomer disclosed below in Polymer 3 satisfies where RA is methyl, Y2 represents a single bond, Y3 represents a single bond, R14 represents an alkanediyl group having 1 carbon where the carbon is substituted with an ester bond, R12 is an acid labile group, a is 1 and b is 0.
Regarding Claims 4-5, the discussion of Claims 1 and 3 are relied upon as above. Hatakeyama further discloses Polymer 3 comprising a repeating unit having a hydroxyl group as seen in the 4-vinylphenol monomer in the structure below.
Regarding Claim 6, 8-10, the discussion of Claims 1, 3-5 is relied upon as above. Nihashi further discloses the photoresist material further comprising a surfactant and organic solvent (Table 3 shows compositions with surfactant and organic solvent, Col 117-118). In addition, Nihashi further discloses compound (C), a photoacid generator, may be a low molecular weight compound or may be incorporated into part of a polymer, and further a form of low molecular weight compound and a form incorporated into a part of a polymer may be used in combination (Col 47, Ln 54-58). Also, the compound (B) (which is equivalent to the quencher) may be used alone or in combination or two or more thereof (Col 47, Ln 25-26).
It would have been obvious for one of ordinary skill in the art to have used the polymer-bound photoacid generator and a low molecular weight photoacid generator in combination and a combination of two or more compound (B) quenchers based on the disclosure of Nihashi through routine experimentation. One of ordinary skill would reasonably expect the addition of a low molecular photoacid generator with a polymer bound photoacid generator and two or more compound (B) quenchers to result in a working resist composition based on the disclosure of Nihashi.
Regarding Claims 11 and 13-15, the discussion of the positive resist material of Claims 1, 3, and 4, and 6 are relied upon as above. Nihashi further discloses patterning process comprising forming the film on a substrate (Col 94, Ln 4-5), expositing the film to actinic radiation such as X-ray, EUV, electron beam (Col 94, Ln 25-30), and developing the exposed resist film with a developer such as organic solvent (Col 94, Ln 60-64).
Regarding Claims 16 and 18-20, the discussion of the Claims 11, 13-15 are relied upon as above. Nihashi further discloses where the radiation is electron beam or EUV (Col 94, Ln 4-5). Secondly, Hatakeyama further discloses the high-energy radiation is i-line of wavelength 365 nm, ArF excimer laser radiation of wavelength 193 nm, KrF excimer laser radiation of wavelength 248 nm, EB, or EUV of wavelength 3 to 15 nm (paragraph [0032]).
Claims 6, 8-10, 15, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Nihashi (US Patent No. 10,788,754) in view of Hatakeyama (US 2021/0048746) as applied to Claim 1, 3-5 and further in view of Lilin (US 2018/0151351).
Regarding Claim 6, 8-10, the discussion of Claims 1, 3-5 is relied upon as above. Nihashi further discloses the photoresist material further comprising a surfactant and organic solvent (Table 3 shows compositions with surfactant and organic solvent, Col 117-118).
Nihashi is silent to examples of the photoresist material further comprising one or more acid generators other than the sulfonium salt and a quencher other than the quencher of the sulfonium salt.
However, Lilin teaches a photosensitive composition comprising a base polymer, a solvent, a photoacid generator, a quencher and an additive (paragraph [0049]). Furthermore, the chemical additive may be a second polymer, second photoacid generator, second quencher, or a combination thereof (paragraph [0049]). Further embodiments describe where the second PAG is different from the first PAG in the composition and where the second quencher is different from the first quencher in the composition (paragraph [0052]-[0053]). The addition of a second PAG and a second quencher both reduce the footing profile and improve critical dimension uniformity (paragraph [0025]-[0026]).
It would have been obvious for one of ordinary skill in the art to have modified the photoresist composition of Nihashi with a second photoacid generator and quencher that are different from the first photoacid generator and quencher. One of ordinary skill would have been motivated to make this modification to reduce the footing profile and improve critical dimension uniformity as suggested by Lilin.
Regarding Claim 15, the discussion of the positive resist material of Claim 6 is relied upon as above. Nihasi further discloses patterning process comprising forming the film on a substrate (Col 94, Ln 4-5), expositing the film to actinic radiation such as X-ray, EUV, electron beam (Col 94, Ln 25-30), and developing the exposed resist film with a developer such as organic solvent (Col 94, Ln 60-64).
Regarding Claim 20, the discussion of Claim 15 is relied upon as above. Nihashi further discloses where the patterning radiation is electron beam or EUV (Col 94, Ln 4-5). Secondly, Hatakeyama further discloses the high-energy radiation is i-line of wavelength 365 nm, ArF excimer laser radiation of wavelength 193 nm, KrF excimer laser radiation of wavelength 248 nm, EB, or EUV of wavelength 3 to 15 nm (paragraph [0032]).
Claims 1, 3-6, 8-11, 13-16 and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Nihashi (US Patent No. 10,788,754) in view of Hatakeyama-2 (US 2018/0004087).
Regarding Claim 1, Nihashi teaches a radiation-sensitive resin compositions (abstract) comprising an acid generator being a sulfonium salt of a sulfonate ion bonded to a polymer main chain (Polymer A-17 on Col 17, Ln 50 as shown below). The actinic ray-sensitive or radiation-sensitive composition comprises a compound (B) which is capable of forming a polar interaction with the polar group of the resin (A’) (Col 42, Ln 6-10). The compound (B) is not particularly limited as long as it is capable of forming a polar interaction with the resin (A’) (Col 42, Ln 15-16). The compound (B) is preferably a compound represented by the General Formula (B1): (Rx)n2–X+ Ry–A- (Col 42, Ln 22-30). A- represents an organic acid anion, X+ represents a nitrogen cation, a sulfur cation, or an iodine cation, Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group, and Rx represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group (Col 42, Ln 30-43). Furthermore, Nihashi discloses that in the description of the present invention, in the case where a group is denoted without specifying whether substituted or unsubstituted, the group includes a both a group having no substituent and a group having a substituent (Col 4, Ln 35-44). Some disclosed examples of the compound (B) are described in the working examples through the compounds B-5 to B-8, shown below, which comprise organic anions of hydroxide anion, carboxylate anion, and fluorinated alkoxide anion and organic cations of ammonium cation, sulfonium cation, and iodonium cation (Col 112, Ln 1-35). The compound B capable of forming a polar interaction with the resin A enables a neutralization interaction that improves resolution and LWR, which is similar to the function of a quencher (Col 6, Ln 12-22). The compounds B-6 and B-8 are both used in exemplified formulations as shown in Table 3 (Col 117-118) that showed excellent sensitivity, resolution, LWR performance, and local pattern dimension uniformity (Col 121, Ln 35-40). Compound B-6 satisfies where R1 represents a phenyl group and compound B-8 satisfies where R2-R4 are hydrocarbyl groups having 4 carbons; this structure satisfies the general formula B1 where Ry is an aralkyl group substituted with fluorine atoms. Compound B-8 satisfies the sulfonium cation where R2 to R4 are hydrocarbyl group having 4 carbons. Nihashi further discloses the Rx groups may comprise alkyl groups of 1 to 20 carbons (Col 43, Ln 10-15), cycloalkyl groups (Col 43 Ln 19-30), aryl groups (Col 43, Ln 31-34), aralkyl groups (Col 43, Ln 35-39), and heterocyclic groups (Col 43, Ln 40-47), all of which may further have a substituent (Col 43, Ln 49-51) (pertaining to the R2 to R4 groups).
Regarding the acid generator, Nihashi further discloses the compound (C) capable of generating acid by actinic rays or radiation is a photoacid generator (Col 47, Ln 45-53), and compound (C) may be a low molecular weight compound or may be incorporated into part of a polymer and further a form of low molecular weight compound and a form incorporated into a part of a polymer may be used in combination (Col 47, Ln 54-58). Nihashi exemplifies one example of a polymer comprising a photoacid generator in Polymer A-17, which is a sulfonium salt of a sulfonate ion bonded to a polymer main chain (Col 107-108).
Nihashi discloses all of the elements of the quencher separately but not disclosed in a single embodiment. The general formula B1 discusses the counteraction of the compound (B) may be a nitrogen cation, a sulfur cation, or an iodine cation. Furthermore, the group Ry may represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group which may have a substituent. Rx groups may comprise alkyl groups of 1 to 20 carbons, cycloalkyl, aryl, aralkyl, and heterocyclic groups. Thus, it would have been obvious for one of ordinary skill in the art to have substituted the ammonium cation of B-6 with the sulfonium cation of B-8 and to have substituted the fluorinated aralkyl group of the anion in B-6 with a fluorinated alkyl group based on the disclosure of the general formula B1 of Nihashi. While Nihashi is silent to the particular number of carbons present in the alkyl group, one of ordinary skill would look towards the simplest alkyl groups, such as alkyl groups with 1 to 6 carbons in lieu of evidence demonstrating otherwise. One of ordinary skill would envision such a modification of B-6 to produce a fluorine-substituted alkyl group such that R1 could be fluorine or an unsubstituted or fluorine substituted alkyl group having about 1-3 carbons.
It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose…[T]he idea of combining them flows logically from their having been individually taught in the prior art. In re Kerkhoven, 205 USPQ 1069 1072. In the instant case, it would have been obvious to one of ordinary skill in the art to obtain a quencher salt comprising the claimed limitation of general formula (1) and arrive at the instant claims through routine experimentation.
Nihashi does not teach the acid generator being a sulfonium salt of a sulfonate ion bonded to a polymer main chain having formula (a1) or (a2).
However, Hatakeyama-2 discloses positive resist compositions comprising a specific polymer which exhibit higher sensitivity and resolution and minimal edge roughness (LER, LWR) and forms a pattern of good profile after exposure (paragraph [0023]). The polymer comprises preferred repeating units having formula d1, d2, or d3 (paragraph [0029], structures on page 3 referenced below). The recurring units d1, d2, and d3 function as an acid generator (paragraph [0081]). Hatakeyama-2 discloses that binding an acid generator to the polymer backbone is effective for reducing acid diffusion and preventing the resolution from lowering due to blur by acid diffusion; additionally, edge roughness is improved because the acid generator is uniformly dispersed (paragraph [0081]). The structure of d2 ([0076]) comprises an acrylate or methacrylate structure where RA may be H or methyl (corresponding to the claimed RA is hydrogen or methyl and Z1 is an ester bond), Y1 is a single bond or a C1-C12 linking group which may contain an ester, other moiety or lactone ring (corresponding to the claimed Z2 being a single bond, a Z21 group with an ester or other moiety having a C1 to C12 hydrocarbylene group), Rf1 to Rf4 may be are each independently F, H, or trifluoromethyl (corresponding to the claimed Z3 being methylene group, 2,2,2,-trifluoromethyl-1,1-ethanediyl group), and R14 to R16 are each independently C1-C20 alkyl that may contain ester, ether, carbonyl, C6-C12 aryl, C7-C20 aralkyl or mercaptophenyl (corresponding to the claimed R5 to R7 being hydrocarbyl group having 1-20 carbons). The structure of d3 [0076] comprises RA is H or methyl (corresponding to the claimed RA being H or methyl), Y2 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene -O-R22-, or -C(═O)-Z2-R22-, Z2 is -O- or -NH-, R22 is a C1-C6 straight, branched or cyclic alkylene group, C2-C6 straight, branched or cyclic alkenylene group, or phenylene group, which may contain a carbonyl, ester, ether or hydroxyl moiety (corresponding to the claimed Z4), and R14 to R16 are each independently C1-C20 alkyl that may contain ester, ether, carbonyl, C6-C12 aryl, C7-C20 aralkyl or mercaptophenyl (corresponding to the claimed R5 to R7 being hydrocarbyl group having 1-20 carbons)
Nihashi discloses the photoacid generator may be bound to a polymer chain and Hatakeyama-2 discloses other polymer-bound sulfonate ion sulfonium salt photoacid generator resins. It would have been obvious for one of ordinary skill in the art to have substituted the onium salt polymer of Nihashi with the onium salt polymer of Hatakeyama-2 through routine experimentation. The onium salt-containing polymers perform the same function as a photoacid generator bound to a polymer chain and their substitution would result in the predictable result of a base resin capable of generating acid upon irradiation to light. Furthermore, one of ordinary skill would have been motivated to make this modification to improve sensitivity, resolution and minimal edge roughness (LER, LWR) and to form a pattern of good profile after exposure as suggested by Hatakeyama-2.
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Regarding Claim 3, the discussion of Claim 1 is relied upon as above. Hatakeyama-2 further discloses that the polymer resin further comprises recurring units b1 and b2 (paragraph [0027] contains the following structural definitions).
The recurring unit b1 comprises RA is methyl or hydrogen (corresponding to the claimed RA is hydrogen or methyl), X1 is a single bond, C1-C14 linking group containing an ester, ether, or lactone moiety, phenylene or naphthalene group (corresponding to the claimed Y1 is a single bond, phenylene, naphthylene, linking group having 1 to 14 carbons containing at least one selected from an ester, ether, or lactone), and R3 is an acid labile group (corresponding to the claimed R11 is an acid labile group).
The recurring unit b2 comprises RA is methyl or hydrogen (corresponding to the claimed RA is methyl or hydrogen), X2 is a single bond, ester bond, or amide bond (corresponding to the claimed Y2 is single bond, ester bond, or amide bond), R6 is a single bond, C1-C6 alkylene group in which at least one carbon may be substituted by an ether or ester moiety (corresponding to the claimed R14 is a single bond, alkanediyl group having 1-6 carbons, and some of the carbon atoms are substituted with ether or ester, and Y3 is a single bond), R5 is hydrogen, fluorine, trifluoromethyl, cyano, or C1-C6 alkyl (corresponding to the claimed R13 represented fluorine, trifluoromethyl, cyano, or saturated hydrocarbyl group having 1 to 6 carbons), R4 is an acid labile group (corresponding to the claimed R12 is an acid labile group), p is 1 or 2 (corresponding to the claimed a is 1 or 2) and q is 0 to 4 (corresponding to the claimed b is 0 to 4), which necessarily satisfies where 1≤a+b≤5.
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Regarding Claims 4-5, the discussion of Claims 1 and 3 are relied upon as above. Hatakeyama-2 further discloses in a preferred embodiment, the polymer may further comprise recurring units (c) having an adhesive group selected from hydroxyl, carboxyl, lactone ring, carbonate, thiocarbonate, carbonyl, cyclic acetal, ether, ester, sulfonic acid ester, cyano, amide, and —O—C(═O)-G- wherein G is —S— or —NH— (paragraph [0072]).
Regarding Claim 6, 8-10, the discussion of Claims 1, 3-5 is relied upon as above. Nihashi further discloses the photoresist material further comprising a surfactant and organic solvent (Table 3 shows compositions with surfactant and organic solvent, Col 117-118). In addition, Nihashi further discloses compound (C), a photoacid generator, may be a low molecular weight compound or may be incorporated into part of a polymer, and further a form of low molecular weight compound and a form incorporated into a part of a polymer may be used in combination (Col 47, Ln 54-58). Also, the compound (B) (which is equivalent to the quencher) may be used alone or in combination or two or more thereof (Col 47, Ln 25-26).
It would have been obvious for one of ordinary skill in the art to have used the polymer-bound photoacid generator and a low molecular weight photoacid generator in combination and a combination of two or more compound (B) quenchers based on the disclosure of Nihashi through routine experimentation. One of ordinary skill would reasonably expect the addition of a low molecular photoacid generator with a polymer bound photoacid generator and two or more compound (B) quenchers to result in a working resist composition based on the disclosure of Nihashi.
Regarding Claims 11 and 13-15, the discussion of the positive resist material of Claims 1, 3, and 4, and 6 are relied upon as above. Nihashi further discloses patterning process comprising forming the film on a substrate (Col 94, Ln 4-5), expositing the film to actinic radiation such as X-ray, EUV, electron beam (Col 94, Ln 25-30), and developing the exposed resist film with a developer such as organic solvent (Col 94, Ln 60-64).
Regarding Claims 16 and 18-20, the discussion of the Claims 11, 13-15 are relied upon as above. Nihashi further discloses where the radiation is electron beam or EUV (Col 94, Ln 4-5). Secondly, Hatakeyama-2 further discloses the high-energy radiation is i-line of wavelength 365 nm, ArF excimer laser radiation of wavelength 193 nm, KrF excimer laser radiation of wavelength 248 nm, EB, or EUV of wavelength 3 to 15 nm (paragraph [0032]).
Claims 6, 8-10, 15, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Nihashi (US Patent No. 10,788,754) in view of Hatakeyama-2 (US 2018/0004087) as applied to Claims 1, 3-5 and further in view of Lilin (US 2018/0151351).
Regarding Claim 6, 8-10, the discussion of Claims 1, 3-5 is relied upon as above. Nihashi further discloses the photoresist material further comprising a surfactant and organic solvent (Table 3 shows compositions with surfactant and organic solvent, Col 117-118).
Nihashi is silent to examples of the photoresist material further comprising one or more acid generators other than the sulfonium salt and a quencher other than the quencher of the sulfonium salt.
However, Lilin teaches a photosensitive composition comprising a base polymer, a solvent, a photoacid generator, a quencher and an additive (paragraph [0049]). Furthermore, the chemical additive may be a second polymer, second photoacid generator, second quencher, or a combination thereof (paragraph [0049]). Further embodiments describe where the second PAG is different from the first PAG in the composition and where the second quencher is different from the first quencher in the composition (paragraph [0052]-[0053]). The addition of a second PAG and a second quencher both reduce the footing profile and improve critical dimension uniformity (paragraph [0025]-[0026]).
It would have been obvious for one of ordinary skill in the art to have modified the photoresist composition of Nihashi with a second photoacid generator and quencher that are different from the first photoacid generator and quencher. One of ordinary skill would have been motivated to make this modification to reduce the footing profile and improve critical dimension uniformity as suggested by Lilin.
Regarding Claim 15, the discussion of the positive resist material of Claim 6 is relied upon as above. Nihasi further discloses patterning process comprising forming the film on a substrate (Col 94, Ln 4-5), expositing the film to actinic radiation such as X-ray, EUV, electron beam (Col 94, Ln 25-30), and developing the exposed resist film with a developer such as organic solvent (Col 94, Ln 60-64).
Regarding Claim 20, the discussion of Claim 15 is relied upon as above. Nihashi further discloses where the patterning radiation is electron beam or EUV (Col 94, Ln 4-5). Secondly, Hatakeyama-2 further discloses the high-energy radiation is i-line of wavelength 365 nm, ArF excimer laser radiation of wavelength 193 nm, KrF excimer laser radiation of wavelength 248 nm, EB, or EUV of wavelength 3 to 15 nm (paragraph [0032]).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KEVIN JAMES DRUMMEY whose telephone number is (703)756-5419. The examiner can normally be reached Monday - Friday 7:30am-5:00pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Huff can be reached at (571) 272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/K.J.D./Examiner, Art Unit 1737
/MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737